The Great Career Reset in the Age of AI | Yamini Rangan, HubSpot CEO

In this episode of Silicon Valley Girl, Marina Mogilko sits down with Yamini Rangan, CEO of HubSpot—a $30 billion company powering millions of businesses worldwide. Yamini shares her journey from arriving in the U. S. with $200 to leading one of the most powerful tech companies in the world. She breaks down the 3 skills companies are hiring for in the AI era, why past success can block future growth, and the "5 Whys" framework that helped her become CEO and lead HubSpot through COVID and a founder transition. We also dive into navigating career uncertainty, knowing when to reset your career, and making decisions under pressure. Topics covered: The 3 skills that matter in the AI eraThe "5 Whys" decision-making frameworkHow to know when it's time for a career resetNavigating career switches and uncertaintyLeading through crisis and unexpected changeWhy your past might be limiting your future More from the Silicon Valley Girl: Newsletter:⁠⁠⁠ https://siliconvalleygirl.beehiiv.com/⁠⁠⁠ https://siliconvalleygirl.beehiiv.com/ Instagram: ⁠⁠⁠https://www.instagram.com/siliconvalleygirl/ ⁠⁠⁠ https://www.instagram.com/siliconvalleygirl/ YouTube: ⁠⁠⁠https://www.youtube.com/@SiliconValleyGirl⁠⁠⁠ https://www.youtube.com/@SiliconValleyGirl LinkedIn: ⁠⁠⁠linkedin.com/in/marinamogilko⁠⁠⁠ https://www.linkedin.com/in/marinamogilko/

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Speaker 00

  This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome, that's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks. Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up required. Compatibility and availability varies 18 plus.

• 0:26Speaker 01

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• 0:55Speaker 02

  Today with AI, there is no map. So you have to get comfortable with being an explorer.

• 1:02Marina Mogilko?

  This is Yamini, CEO of HubSpot, a $30 billion company. She arrived in the US in her 20s with a few hundred dollars in her pocket. And now she's running one of the most powerful tech companies in the world. You land in Silicon Valley, which is mostly male, right?

• 1:18Speaker 02

  I still feel it. I go into some rooms and I'm like, can I do this?

• 1:23Marina Mogilko?

  She navigated her way in a dot com crush.

• 1:26Speaker 02

  First day of my job, they laid off half the class.

• 1:29Marina Mogilko?

  Years later, she joined HubSpot and almost immediately, everything breaks at once. Covid hits and a year later, the founder and CEO Brian Halligan had a snowmobile accident.

• 1:41Speaker 02

  And he called me from the hospital and he was like, look, I need time to recover. So just run the company. I was like, really? What do I do? And he's like, don't screw it up.

• 1:50Marina Mogilko?

  She steps in to run the company.

• 1:53Speaker 02

  A lot of people think functionally. I started in sales. Now I'm going to become a senior manager and then I'll become a director. That is great if you want to be just in a function. But sometimes things that got us here are not enough for us to get to our path forward.

• 2:09Marina Mogilko?

  Can you give advice to someone who feel like they've plateaued in their career? What is the one thing that they should change right now to start growing?

• 2:18Speaker 02

  Okay, first off.

• 2:21Marina Mogilko?

  Yamini, you have an amazing story. You arrived in the US in your twenties with a few hundred dollars in your pocket.

• 2:28Speaker 02

  Yep.

• 2:28Marina Mogilko?

  Now you're running a multi-billion dollar company as a CEO. For anyone who doesn't know you, can you talk about your background and career shortly?

• 2:36Speaker 02

  Yeah, I grew up in India and a family of, you know, two girls. I know you have two girls. We grew up in a super small town, so we should not have, you know, been dreaming big. But my mom was just, you know, amazing. And she really helped us think beyond our little town, our little school. The school didn't go all the way till, you know, 12th. So she moved to a different city to make sure that we got an education. And look, I think Marina, if someone takes you seriously, you begin to take yourself very seriously. And so that was a huge thing. So the rest of the story is I did come here after my undergrad in electronics engineering. I came here, I did a master's in computer engineering, worked as an engineer for a handful of years.

• 3:21Speaker 02

  And then I was still searching for something. I was like, ah, this is, this is not the thing and I want to do something more. And so, you know, as everybody who doesn't quite know exactly what they want to do, I went to business school.

• 3:32Marina Mogilko?

  Oh, yeah.

• 3:33Speaker 02

  And I went to business school here in Berkeley. And I graduated literally at the worst time because it was right after dot com bust. My first job after business school was Siebel Systems. The first day of my job, they laid off half the class. And then they said, they somehow looked at me and said, you should be in sales. And I was like, sales? Okay, I have no idea what I will be doing, but that's how I got started in sales. And then the next decade was at companies like Workday and Dropbox, which was incredible experience of being very cross-functional in nature. So I went from sales to sales strategy and operations and then marketing and customer success. And then I landed at HubSpot in 2020.

• 4:20Speaker 02

  And it was crazy times, but I will tell you that that's nutshell. My career started as an engineer, went into sales and then went into multiple customer facing roles and have just enjoyed every bit of it.

• 4:32Marina Mogilko?

  I love it. I love that you changed so many roles and positions in companies, especially as an immigrant. Can you walk me through like one of the hardest transitions that you had to make? And what was your mindset back then? Like, yeah, I'm gonna quit this company and do this.

• 4:45Speaker 02

  Well, mindset is a really important, you know, kind of like word because you have to have a growth oriented mindset to figure things out. I mean, here I was newly minted MBA and I was in the sales organization. I had like a quota and, you know, Marina, I looked around the room and there were not that many Asian women in the sales organization at that time. And initially, I kind of like looked at that and I said, who's the successful person here and how do I kind of become them? Turns out they were all men playing golf and they were incredible at their job,

• 5:26Speaker 02

  but they were also exceptionally extroverted and they had like a method about that. And I was like, you know, I'm an engineer, introverted, Asian woman. And I'm like, I'm gonna try that. So I tried their approach, right? Of trying to sound extroverted, not, you know, trying to play golf, trying to learn sports, none of that worked for me. So I was like, you know what? This is not what I'm gonna do. So I, there was a moment where I decided I'm so bad at what others are doing so naturally. So let me do what comes naturally for me. And for me, I was analytical. I was a deep thinker, you know, I liked businesses.

• 6:09Speaker 02

  I was curious about people's businesses, people's careers. And so I said, you know what? I'm going to really be the kind of person who asks deep questions about the, the company and their business and what they want to accomplish. So that was a big shift. And I started enjoying it because it was tapping into what I was naturally inclined to versus trying to find someone else's playbook. And pretty early in my career where I said, you know what? I need to stand out. As myself authentically versus trying to fit into this room, fit into what others are doing. And I think it was a huge lesson. I've taken it forward.

• 6:50Marina Mogilko?

  It's amazing and it's such a great lesson for everyone listening because it happened to me as well. You know, you land in Silicon Valley, which is mostly male, right? Still mostly male. You're like, do I fit? Can I do it like them? Do you still get this feeling ever? Like when you walk in the water?

• 7:06Speaker 02

  I still feel it. I go into some rooms and I'm like, can I do this? And that is natural. And I think that it's it's healthy even because it actually pushes you not to just sit in the doubt and uncertainty, but to find a path forward. And the way I've found it works is instead of saying, can I do this? You know, can I crack this particular project or initiative or role or new company that I'm part of? I always start about look at the future and create the future that I want. So I always think like three years, you know, from now. And I say, okay, what should I be really happy to have accomplished? And let me work backwards from that.

• 7:50Speaker 02

  So then it stops this feeling of can I do it? And really focuses you on exactly what you're trying to accomplish. Then you map all your actions and where you spend time and what you are really prioritizing towards those actions. And then all the doubts kind of go away. But you know, the thing is it never goes away.

• 8:35Marina Mogilko?

  Yeah, it's just basically focusing on your learned term goals and focusing on them versus comparing yourself.

• 8:41Speaker 02

  Comparing or feeling like your past, you know, the biggest learning for me was don't look at your past to predict what you want to do in the future. Look at the future to create the kind of patterns that you want right now.

• 8:54Marina Mogilko?

  Interesting. Do you ever have a feeling like, oh, my past is what got me here?

• 9:00Speaker 02

  Yeah.

• 9:00Marina Mogilko?

  So if I change, I might not be as successful because I don't know, like I get grounded, I did this, this and that.

• 9:06Speaker 02

  Yes, but sometimes, you know, things that got us here are not enough for us to get to our path forward. So there are times when if you just look at your past playbook and things that have worked for you, it's not enough. It's not enough to where you're going. And so there are times when past is just limiting. There are times when past will just, you know, only add doubts to your capabilities, not energy towards something that you want to create. And so for me, it's, it's, I don't lose lessons from the past, but I also don't just bank on the past for my future success. You just create it.

• 9:49Speaker 02

  You just create it and you put your intent and the set of actions. And to me, it's super practical, Marina. I do have what I want to accomplish, you know, in three years and I update it every year at the end of the year. I'm kind of like reflecting on where I made progress and I write it and I have like top three goals. And mostly during the year, I'm looking at those goals on a weekly basis and, you know, is my calendar reflect those priorities? Am I actually spending the time improving my skill set to get to those priorities? So it's actually very practical in the, in terms of where I'm looking to go and, you know, really puts away all this doubt and, you know, the way we get limited by just kind of what we have accomplished in the past.

• 10:34Marina Mogilko?

  That's amazing. I think that's a great tip for a lot of immigrants.

• 10:38Speaker 02

  Yes.

• 10:38Marina Mogilko?

  Who are like, I've done this in my country, but it's not going to work here.

• 10:41Speaker 02

  Yes.

• 10:42Marina Mogilko?

  Because it's different. And then Yemeni, you've done so many. Different things. You've done sales, you've done strategy, customer success. How do you convince someone you're good at something you haven't done before? Like with sales, right?

• 10:53Speaker 02

  Yeah, I think I had doubts, like any twenty something, thirty something would have. I had like a lot of doubts. I started in sales and I did that for almost a decade, Marina. Then I had two kids and both of them were under three. And we had two careers in the family, both crazy. And I'm like, this is not sustainable. Uh, so what can I do with my skill set of what I have done in the last like decade? And then I was like, strategy and operations, because I understand, you know, being in front of customers. I understand how customers think, negotiate, buy. And now I can use that to kind of like, uh, help companies scale.

• 11:37Speaker 02

  And where do you put in the right resources? How do you support salespeople? I can do all of that, those. And so that pitch was easy. Once I did that, uh, then I found that connecting the dots was just exceptionally important as a skill. And what I mean by that is, a lot of people think functionally. I started in sales, now I'm going to become a senior manager, and then I'll become a director, and then I'll become a senior director. And they're kind of like going through that. That is great if you want to be just in a function. What is also fascinating is if you can connect the dots across multiple functions. In strategy and operations, I learned how important marketing and sales interlocking on their strategies was.

• 12:21Speaker 02

  And so I helped marketing teams, you know, talk to sales teams to come up with common strategies. So I think later in my career, I was able to like connect the dots, um, and bring insights that teams were generally missing being in silos. And the ability to connect dots and, you know, I call it the T-zone leader. Go deep in a couple of functions and go broad across multiple functions. And you have to have some functional orientation to have depth. But then later on in your career. It's all about being a T-zone leader, connecting the dots across multiple functions, really solving first for the customer, you know, not even for your function or your company,

• 13:04Speaker 02

  first for the customer, then for the company, then for your function, and then for yourself. And if you have that mental model, then new roles open up and new opportunities open up.

• 13:16Marina Mogilko?

  This is fascinating, the shift you talked about, like how you thought, okay, I want a sustainable career to have a family. Did you ever have regrets that because you're now a mom, you have to go through this change?

• 13:28Speaker 02

  Yes, of course.

• 13:30Marina Mogilko?

  So that transition didn't happen easily, right?

• 13:33Speaker 02

  I mean, we all have doubts. I mean, you know, looking back, you can see the things that worked and the things that didn't work.

• 13:39Marina Mogilko?

  For now, it looks like such a good strategic move, right?

• 13:42Speaker 02

  Oh, yeah, but at that time, I was like, why is it that I am the one who has to, you know, take a backseat? Why is it maybe like these people who are just, you know, still doing sales, they're going to like progress? And, you know, you, you're trying to figure your life and you don't know if all of the decisions you make are actually going to add up to something good. And this is the thing about being in your twenties and thirties is that you have to have a certain set of principles of what you want to do. I do think that I wanted to be there for my family. I wanted to be there for my kids and be part of the time that I was spending in front and with them.

• 14:26Speaker 02

  At the same time, I didn't know it was going to play out. And I had regrets along the way of, am I doing this right thing? You know, is this the right move for me? And you don't know. And a little bit of uncertainty is what you'll have to live with as a mom, as a career professional, navigating multiple careers and multiple kids. You just have to navigate that and it's hard. Don't assume that people know exactly what they're doing. And it's kind of okay if you don't know every bet that you make. As long as you know what your priorities are at any given point and you have a way of sorting through. What those priorities are, that can ground you. But you don't know if it's all going to lead to anything, you know.

• 15:11Marina Mogilko?

  And it all played out well for you, right? So you became the CEO of HubSpot first interim, then permanent CEO. What do you think made the board say she's the one?

• 15:21Speaker 02

  I don't know.

• 15:23Speaker 02

  But but here's here's what I will give you about that journey. So I joined HubSpot in January twenty twenty. And initially Brian Halligan, who's was the CEO at that point. He's the co-founder of the company, incredible mentor. You know, initially he was like, take all your time, you know. Take your time, talk to customers, you don't need to make any changes. March twenty twenty hit. You know what March twenty twenty was. It was obviously the world shut down, but also for small, medium businesses. That is, the our customer base that we were serving, so much uncertainty and so much churn. And we started seeing customers like didn't know what to do.

• 16:05Speaker 02

  So they were like stopping their businesses, businesses bent out, bankruptcy, all of this stuff. And he looked at me and he's like, do something, you know. And I need something that we can go and talk to our board about. I pulled our team together. We had a great leadership team within the go-to-market organization. That's the team that I was leading. And I I said, OK, we're going to meet every day for a couple of times a day, morning and evening. And I want all of your best ideas. And any crazy idea that you would never have done before, because it was not the time or we couldn't have pushed it, let's just do it. And so we started making all these crazy ideas. And the list was, Marina, really crazy.

• 16:45Speaker 02

  It was take your product and cut the price by seventy five percent and give it away to customers because they all need digital tools. Take features that were pretty expensive and move it to free because now customers needed to use digital marketing. They needed to do inside sales and they needed to support digitally. So we did all of that. So we went to the board and we said, we're going to cut the price by seventy five percent. We're going to take a lot of features and move it to free tier. And then we're going to create a fund for customers and call it the Customer Relief Fund. And anybody who feels like they cannot pay for the next six to nine months, which is going to give them the benefit of doubt.

• 17:28Speaker 02

  And we're going to use this Customer Relief Fund to help support them. And the board said, okay. How are you gonna get this money back? I literally said to them, I don't know. This is the first time, but I'll tell you what. We've always said our North Star is solving for the customer. Our customers are really at this point where they don't know what to do and we're just going to help. And we hope the goodwill will pay something forward. And it did. So March was terrible, April was terrible, May was terrible. Towards the end of May, people started buying. And then June, second half of 2020, everybody wanted to get digital tools to market, sell, support, and reach their customers.

• 18:13Speaker 02

  People who didn't have websites needed websites. 2020 and 2021, it was just massive acceleration. And so you asked this question. So Brian did have, you know, unfortunate snowmobile accident in March 2021. And he called me from the hospital and he was like, look, I need time to recover. So just run the company. And I was like, really? What do I do? And he's like, don't screw it up.

• 18:41Marina Mogilko?

  No pressure.

• 18:43Speaker 02

  Don't screw it up and don't call me because I really need to recover. And he did need the time. And frankly, I think that doing the right thing for customers and making some bold calls where you don't know the answer, but you have high conviction on the path. I think that worked. And so by the time Brian came back in August, I'd done this for a little while. And I would say that if I asked him now, if I asked the board, they would say that you took bold actions and those actions turned out to be the right thing for the customer and it was the right thing for HubSpot. And so we built enough confidence that you can continue to execute.

• 19:26Speaker 02

  And so, yeah, it comes down to, do you have a North Star?

• 19:31Marina Mogilko?

  Priorities again.

• 19:32Speaker 02

  Principle, yes. A set of principles that you can count, you know, on yourself to make the decisions. And can you do it? You know, if you need to make a decision five minutes, five days, you know, quickly, can you use those first principles to make the decisions? And then do you, can you take a little bit of risk to, you know, have a point of view and then really make that happen? And if you can do those, then opportunities do open up. I'm super grateful. It's just a privilege to lead a company like HubSpot since then.

• 20:08Marina Mogilko?

  It's again, like going back to your principles, having a North Star, having a big goal in mind and acting from it.

• 20:15Speaker 02

  Yep.

• 20:15Marina Mogilko?

  So from the operational standpoint, being this AI-first company, what does it mean from, for your day to day?

• 20:22Speaker 02

  I do think that because of AI, we are building things differently. We are selling and providing services to customers differently and we are working differently. This year, and we're talking in 2025, this year, you know, ninety-five percent of the codes that our engineering teams have committed came with AI assistant. So compare that to 2023, we were actually writing code. So it requires a pretty big shift, both a cultural shift and a technology shift in terms of how we build products, and that is the shift that we have made. And then how do we market, sell and support customers?

• 21:06Speaker 02

  A lot of the prospecting that we do is with intent data as well as AI intelligence. Our reps, when they go and talk to our customers, they have intelligence of the past hundred conversations they've had, similar customers they've talked to, what objections they should expect, who they're talking to. All of that is within their fingertips. And so we've really changed how we interact with customers and then how we work internally. When we think about work, we think about what can be automated with AI, what can augment the productivity of teams and how can we do things better? And so, look, I think, you know, somewhere last year, there was just this debate of AI is all about efficiency. It's going to like cut jobs and it's all.

• 21:52Speaker 02

  About efficiency, we at HubSpot had a very different view. We said, this is the way of the future, which means that every HubSpotter needs to learn and we need to use these tools ourselves. We need to experiment with a lot of these tools so that we can have high conviction when we communicate with customers. So it was more of a, let's inspire the team to learn.

• 22:16Marina Mogilko?

  Yeah.

• 22:16Speaker 02

  And therefore serve customers better. And I'll tell you, like, people send me slacks with, uh, here's what I created and here's a demo. And they're actually excited about learning. And when you create that culture of learning and growing and experimenting, then get the AI first or AI native, you've really changed the way you work. And that is what is important right now.

• 22:42Marina Mogilko?

  Yeah, and I like how you noted that. And I'm feeling this now, like last year, all the headlines were like, AI is taking your job. Now we're like, we've used the tools, right? It's not really taking our job, it's making it easier, it's making us more effective, gives us more context.

• 22:58Speaker 02

  Yes.

• 22:58Marina Mogilko?

  But I haven't seen a tool that does the job end to end without me having to check or having my team like.

• 23:05Speaker 02

  Totally, totally. I mean, two years ago, I, you know, come from San Francisco airport all the way to home. They'll be like, hire AI agent.

• 23:14Marina Mogilko?

  I think it's still somewhere around, but less. Have you, I, I have.

• 23:17Speaker 02

  It's less, right? It's less. And now, you know, our perspective has been, future is hybrid.

• 23:23Marina Mogilko?

  Yeah.

• 23:24Speaker 02

  It's going to be humans and agents in the loop, taking all the intelligence that agents and AI can deliver, making ourselves much more productive and doing higher value work. And when we do that, the overall productivity within the organization goes up. But we are also able to translate that into wins for customers. And so we're believers in the future is hybrid with humans and AI in the loop.

• 23:49Marina Mogilko?

  One hundred percent. Yeah. And I remember the, the billboards said, uh, said, um, stop hiring humans here, something like that.

• 23:55Speaker 02

  Exactly.

• 23:56Marina Mogilko?

  Startup. I'm like.

• 23:57Speaker 02

  I have a picture of it. I took the picture.

• 23:59Marina Mogilko?

  Yeah, I have multiple pictures of that. My audience was freaking out when they saw this. Um, if you were advising an entrepreneur right now, what would you tell about like one feature, one AI feature they have to integrate in their processes to feel this amazing power of AI?

• 24:17Speaker 00

  This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome, that's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks. Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up required. Compatibility and availability varies 18 plus.

• 24:42Speaker 02

  So the advice I would give is do not start with an AI feature.

• 24:48Speaker 02

  Start with your business. What is the biggest problem that you're trying to solve? Start with that, and why have you not been able to solve it? And when you start with that, then you identify the right use cases to leverage AI. What is happening is that people are like, oh, use AI for this and use AI for that. And when I have customer conversations, I always ask them, next year, you're looking to grow. What is the biggest obstacle for you to grow? And they will say something like, we don't have enough top of funnel leads. Great, use AI.

• 25:26Marina Mogilko?

  That's your prompt.

• 25:27Speaker 02

  To generate top of funnel leads with better personalization. That's the place to start. Or they'll say, I have hired enough salespeople. They're just not productive, and I want to make them efficient. And the deal process is broken. I don't have enough visibility. Start there. Use prospecting to be able to improve the level of intent information you can get so that your reps can reach out to more accounts at the right time. So my push is, if you're an entrepreneur, if you're a builder, if you are driving a company strategy, start with the biggest problems, and then look for AI features and opportunities. Don't do it the other way.

• 26:10Marina Mogilko?

  Yeah, because otherwise you just spend hours and hours trying different tools without really understanding what the KPI should be, right? What's the metric? What makes this tool successful? If it's not solving a real problem. So start with a problem. Love that. So when you're hiring these days in the AI era, what are the... Two to three skills that you're looking for in a candidate.

• 26:29Speaker 02

  Yeah, it has changed pretty dramatically. And the way I would frame it, we are looking for explorers. And I'll tell you what that means. In a, I think there's a fundamental shift that's happening with AI, where not everybody knows exactly how to go from point A to point B. You know, if you knew exactly and think about them as map readers, right? You know exactly what point A is, point B is. You read the map because someone has figured out the path and you follow the directions and you get there. That is what we were doing because you had playbooks that worked and you were, you know, really clear about following the playbook. Today with AI, there is no map.

• 27:08Marina Mogilko?

  Yeah.

• 27:08Speaker 02

  So you have to get comfortable with being an explorer. And there are a few skill sets that are important. The first one is that you have to have almost a scientist mindset. And I look for people who are comfortable experimenting and having a hypothesis, proving if the hypothesis is right or wrong versus saying there is a set path, right? Like experimentation, moving quickly, having a hypothesis and proving whether you're right or wrong. That is like skill number one and I look for examples of when they have done it or how they have comfort around it. That's like number one thing that I look for. The second is just this passion and curiosity to go deep in the work.

• 27:51Speaker 02

  What is happening is that in order for AI to be effective, you gotta be close to the ground. You have to know what parts of the workflow are broken, what parts of the workflow can actually get value from AI. And you gotta get like really close to the ground, you know? And I talk to customers, but we also do a Gamba walks. We look at like how people are using different technology. I'm looking for people like that who are very close to the ground, close to the process, who can actually make changes. That's the second one. And then the third is really what, you know, I would say as just curiosity and customer orientation. Again, my focus has been, don't forget about AI. Use it.

• 28:37Speaker 02

  To solve something for your customers. So can you be super curious and ask the right questions of, you know, your customers to get the right thing. And if you have the ability to experiment, the ability to stay close to work, the ability to stay curious, then you're actually going to thrive in the world of AI. If you are stuck with your playbook, if you are very comfortable with going from point A to point B in a path that someone else has prescribed, then you're just not going to be successful in the world of AI. That's what I'm looking for.

• 29:06Marina Mogilko?

  Yeah, totally. Do you feel like you're still looking at their education or it's less important now?

• 29:13Speaker 02

  I mean, no, I don't think I have ever looked at just education, because that's just one thing, right? And it is, it's important to be like technically qualified, you know, if you're building product, you need to have the, the basic capacity and everything, but education is just part of the picture. It's all of these intangibles that I'm looking for.

• 29:35Marina Mogilko?

  Yeah. Do you still feel people should pursue higher education or?

• 29:39Speaker 02

  You know what? This is a very controversial topic.

• 29:42Marina Mogilko?

  Yeah.

• 29:42Speaker 02

  I'm all in on education.

• 29:44Marina Mogilko?

  Yeah.

• 29:45Speaker 02

  And so I just dropped my son in freshman in college. As he was about to go, about like four years ago, he said, I want to do computer science and math. And he stuck to it. And so he's studying computer science and math. And all of our friends were like, that is such a wrong, you know, thing. You shouldn't be sending him to study computer science and coding is gone. And I was like, yeah, but who said computer science or math or any of this is about a skill of coding? It is how you think.

• 30:15Marina Mogilko?

  Yeah.

• 30:16Speaker 02

  It is how you learn. It's how you break down problems. And, you know, interestingly, when I graduated from business school, now I'm dating myself multiple decades ago, there was no job called Chief Customer Officer. That's what I eventually ended up becoming. There was no job. So every decade as things evolve, new jobs will evolve. You can't even plan for a job that's going to be there 10 years from now, 20 years from now.

• 30:42Marina Mogilko?

  Even two years.

• 30:43Speaker 02

  Two years from now, but what you can is learn how to think. Learn how to break down problems and solve problems and learn how to ask questions. And if you can do those things, then you know, education is really worthwhile. And that's kind of like, I told my son, yep, you, you should do all of this, whatever you want. But also go deep. If he ends up wanting to do like a graduate program or even go deeper, I'd be all in for that. Just go deeper into an area rather than spread yourself.

• 31:14Marina Mogilko?

  Yeah, just go explore and learn how to learn.

• 31:17Speaker 02

  Exactly, exactly.

• 31:18Marina Mogilko?

  Quick pause here. If you're enjoying this podcast, you will absolutely love my inner circle newsletter. So what I basically do is I take all the tips from these podcasts and I apply them to my personal life, to my investment portfolio and to my businesses, this media company and my language teaching business. Sometimes we get amazing results and I share our real tactics. Sometimes we don't and I share that too. Think of it as an insider version of this podcast. The link is in the description. Join my free newsletter to stay ahead. Is there a decision-making role that you follow as a CEO that someone could learn from you?

• 31:53Speaker 02

  That's a difficult one. It really, first of all, in, in a role as a CEO, in a role as a, you know, C-suite leader, only the most difficult decisions come to you. Sometimes people who are like early in their, you know, leadership career or, you know, in the C-suite, they're like, oh my God, these are all tough problems. I'm like, guess what? Yes.

• 32:14Marina Mogilko?

  Yeah, that's your job.

• 32:15Speaker 02

  Only tough problems come to, come to you. I do think that you have to have some set of principles that you kind of look for. In, in our case at HubSpot and certainly in my personal philosophy, it's always having a north star for the customer. That has been one. I think the second probably is, you know, balancing short-term versus long-term, which a lot of leaders find exceptionally hard to do. And you have to be able to like balance short-term versus like long-term decision-making. And you have to be able to set a vision for slightly long-term. And there is, it's a balance. I don't think it's an easy decision-making framework. It is a balance of some things you have to do that.

• 32:58Speaker 02

  Give results immediately. Some things you have to have the foresight to see how it'll play out over the next couple of years and your job is to balance both.

• 33:06Marina Mogilko?

  It's it's interesting, but also like making decisions where when there's so much fear, right?

• 33:11Speaker 02

  Yeah.

• 33:12Marina Mogilko?

  When it came to COVID, right?

• 33:13Speaker 02

  Yeah.

• 33:14Marina Mogilko?

  The lockdown and then AI. Any anything that like calms you down, like is that the North Star?

• 33:20Speaker 02

  Yeah. First of all, operating from fear is never a good place to operate from. You will make poor decisions.

• 33:30Speaker 02

  Operating from principles, being grounded in a in certain set of principles, but also certain ways in which you operate with, you know, enough peaks and valleys, that is important. So I think like for me, I do think that clear breaks where I'm thinking about something else is important. You know how they talk about peak performance? Of athletes, when you are in flow, when you are in peak performance. The thing that people don't talk about is that they have a period of deep rest. And you can't operate in peak performance. You cannot be operating in a peak decision making skill set without having clear ways of grounding.

• 34:13Speaker 02

  For me, it is like rituals that I have, like, you know, every evening between five thirty and six thirty, I take an hour off. And I listen to music, I listen to podcasts, I listen to something that is not related directly to my work and that disconnects. And then I do take, you know, clear breaks, you know, whether it is vacations with family or something. But I think we underestimate the impact of things that ground.

• 34:41Marina Mogilko?

  We do, especially as immigrants.

• 34:43Speaker 02

  Because we all want to work harder and get to the next thing.

• 34:47Marina Mogilko?

  That's how we were raised.

• 34:48Speaker 02

  But you got to recognize that peak performance comes through peak valleys of rest and, you know, and you have to be able to do both. And for me, those practices have grounded myself. I mean, I make better decisions when I get seven hours of sleep. You know, I I make better decisions when I've had some level of clarity after I do yoga or meditation. And those are as important as the days that I spend grinding, you know.

• 35:16Marina Mogilko?

  I love it. Yeah. When if someone listening to this and is also like, I want to ask you this question because you talked a lot about principles. How do you come up with them? What questions do you ask yourself? Do you have like any, any questions in mind that you should ask yourself to come up with a set of principles? To make those decisions better?

• 35:33Speaker 02

  It's a, it's a really good question. I think for me, practice of reflection has worked. Where over the years, I've always been introspective, somewhat critical of myself. Probably the most critical of myself. And as I reflect and, you know, I'm super critical of myself, I always am like, what did I learn from this? And what would I do differently? And I use every year as a reflection period to say, what did I learn? And what would I take away? And over a period, if there's a pattern emerging that every decision, if you put your customer at the top, it's always going to be the right one.

• 36:14Speaker 02

  That comes because you're reflecting on things that worked and things that didn't work. And for me, having a practice of introspection and really thinking about what did I learn from this year's experience? What worked, what didn't work, what would I take forward from here? That has revealed, you know, patterns, both small in terms of like making, you know, quick decisions within the business, but also fairly large principled, you know, decisions.

• 36:44Marina Mogilko?

  I love it. That's, that's awesome. And I feel like you can also use AI for that. I've been using AI to just-

• 36:49Speaker 02

  Have you?

• 36:50Marina Mogilko?

  I've been brainstorming a lot of decisions with AI.

• 36:52Speaker 02

  Yeah.

• 36:53Marina Mogilko?

  And now I can just ask questions, if you could give me advice, uh, six months ago, what would it be? Based on all of the problems that I experienced and tried to solve with you.

• 37:01Speaker 02

  Yeah.

• 37:01Marina Mogilko?

  And it was super clear.

• 37:02Speaker 02

  That's awesome.

• 37:03Marina Mogilko?

  This is what you prioritize, this is what you struggle with.

• 37:06Speaker 02

  Yeah.

• 37:06Marina Mogilko?

  This is what you should be doing.

• 37:08Speaker 02

  There you go. I haven't, you know, I've kind of created a personal style, you know, for AI, where I talk about the tone and what my values are. Uh, even when I write, I'm like, you know, I don't want any fluff. I want direct, candid communication. The communication needs to feel human, you know? No offense, AI, I don't want like random fluffy words. And I give all of that. And I think over time it learns, but you know, now I'm curious, I'm gonna try and use a lot more of my principles as we make through, make decisions.

• 37:43Marina Mogilko?

  Yeah, I learned this from Mustafa Suleyman. He tells me that every night, uh, he talks to his AI. Just like reflecting on his day, so basically documenting, but with AI. And this way, AI understands the decision-making process, what makes him sad, what makes him happy. So the next time he has a question, AI already comes up with anecdotes from the past, like, oh, you did this. You felt that, so here's how you should probably tackle this. I think it's genius.

• 38:08Speaker 02

  I love it, I love it. I try and do the reflections, but not daily, that's a great practice. And you could probably do it in like five minutes.

• 38:16Marina Mogilko?

  Even if it's weekly, right? If it's some decision-making with AI, I think it's, it's a great practice.

• 38:21Speaker 02

  I love it.

• 38:22Marina Mogilko?

  Can you give advice to someone, or to yourself, a 21-year-old self, arriving in the US, but in the AI era?

• 38:29Speaker 02

  Okay, first off, I'm happy that I arrived when I did, because there is a lot to sort through right now. Which careers are going to survive, which ones are not, what jobs, what should I study? And, you know, are the entry-level jobs going to go away? There's just a lot of uncertainty right now. So I'm actually glad that I came here in, uh, in the 90s when I did, and I've learned so much. And, but on the, on the advice, like, you know, I do think that we started the conversation, Marina, about feeling uncertain about decisions and carrying a lot of anxiety about the future.

• 39:11Speaker 02

  I mean, you come here as a first-generation immigrant, and you come here as a woman, and you look at the rooms that you're in, and there's just a tremendous amount of, am I going to make it? You know, is this decision right? Uh, am I headed in the right way? There's just daily anxiety. And I would calm myself down if I could to go back and be like, you will have some level of anxiety, but just like, you know, enjoy the journey a lot more. And if you have certain principles that you use in your decision-making process, you're going to be fine.

• 39:48Marina Mogilko?

  Yeah.

• 39:49Speaker 02

  And I think there's just a lot more anxiety in me, you know, uh, early in my career. And I would say, you know what? Life will work, it work itself out.

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• 40:53Marina Mogilko?

  Yeah, yeah, trust yourself, basically, right? Because we don't have a lot of trust in ourselves, especially in our 20s.

• 40:58Speaker 02

  That's right.

• 40:59Marina Mogilko?

  Yeah.

• 40:59Speaker 02

  That's right.

• 41:00Marina Mogilko?

  My last question would be,

• 41:01Speaker 02

  Okay.

• 41:02Marina Mogilko?

  Can you talk to people who feel like they've plateaued in their career or in their business? What is the one thing that they should change right now to start growing?

• 41:13Speaker 02

  Ask yourself five ways. Why have you plateaued? Why is something not working for you? Why? Ask five questions of, you know, why, why, why? And be curious about what is the reason? And that is what is going to lead you to something, you know, incremental from where you are. A lot of times, people take superficial answers, both of themselves and of our business, and they wallow in, you know, where they are stuck at, instead of really digging deep and trying to get to the bottom of, why am I in this plateau?

• 41:57Speaker 02

  Well, because I don't know what to do with my job. Why, you know, is that job feeling like you're stuck? Well, because I'm not learning as much. Why am I not learning as much? Because I don't have the right problems to focus on. Why do you not have the right problems to focus on? Something like go deeper and deeper into the why? And the answer will be right there. And the answer is going to be part of you digging deep and understanding why you're stuck and being honest about those answers. Sometimes we don't want to hear the answers. You might be running in a business which is probably going nowhere because there is no market.

• 42:40Speaker 02

  Sometimes we don't want to take that honest answer that we know in our mind. We know in our gut is the honest answer. We don't want to take it, but you got to have the stomach to take that. And then make the change that that is needed, whether it's personally or for your business.

• 42:56Marina Mogilko?

  Yeah, and maybe you dig deeper and you realize your career has nothing to do with your principles or your North Star.

• 43:01Speaker 02

  Yes, exactly, exactly.

• 43:03Marina Mogilko?

  Thank you so much, Yamini. This was so insightful. I feel like I've learned a lot. The thing that I'm going to do after this interview, I'm going to talk to my AI about my principles. We need to figure them out and like set the goals for the next three years.

• 43:16Speaker 02

  There you go. Thank you so much. We're going to appreciate this conversation.

• 43:20Speaker 04

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• 44:18Marina Mogilko?

  Thank you.